Hydrocinnamonitriles

ABSTRACT

WHERE R, R1, R2 and R3 are defined as follows: R is halo, loweralkyl (C1-C4), loweralkoxy (C1-C4), cyano, nitro, trifluoromethyl, phenylazo or p-chlorophenoxy; R1is hydrogen, halo, trifluoromethyl or loweralkyl (C1-C4); R3 is hydrogen or halo; and R2 is phenyl, halophenyl, dihalophenyl, alkyl (C1-C4) phenyl, loweralkoxy (C1-C4) phenyl, 1-naphthyl, 2-furyl, or 2thienyl.   The present invention relates to insecticidal methods and compositions employing Alpha , Beta -dioxohydrocinnamonitriles having the formula:

United States Patent Wright, Jr. et al.

HYDROCINNAMONITRILES Inventors: Donald Perry Wright, Jr.,

Pennington; Donald Frederic Barringer, ,lr., Trenton; Donald EdwardMcKay, Highland Park, all of NJ.

American Cyanamid Company, Stamford,- Conn.

Filed: May 21, 1973 Appl. No.: 362,617

Related US. Application Data Division of Scr. No. 250,338, May 4, 1972,Pat. No. 3,793,456, and a continuation-in-part of Ser. No. 141,444. May7, 1971, abandoned.

Assignee:

U.S. CL... 260/465 E; 260/332.3 R; 260/347.7;

424/275; 424/285; 424/304 lnt. Cl. C07c 121/78 Field of Search 260/465 EReferences Cited UNlTED STATES PATENTS 2/1972 Buchel et al 260/465 Apr.29, 1975 Primary Examiner-Lewis Gotts Assistant Examiner-Dolph H.Torrence Attorney, Agent, or FirmHarry H. Kline ABSTRACT The presentinvention relates to insecticidal methods and compositions employing a,,B-dioxohydrocinnamonitriles having the formula:

Ra ll 5 Claims, No Drawings HYDROCINNAMONITRILES This is a division ofapplication Ser. No. 250,338, filed May 4, 1972, now US. Pat. No.3,793,456, issued on Feb. 19, 1974, and a continuation-in-part ofapplication Ser. No. 141,444, filed May 7, 1971, now abandoned.

The present invention relates to the use of certain hydrazones ininsecticidal methods and compositions. It further relates to certainnovel hydrazones used therein and to the preparation thereof.

More particularly, the invention relates to insecticidal methods andcompositions employing hydrazones of a, B-dioxohydrocinnamonitrileshaving the formula:

NHN=C 1 where R, R R and R are defined as follows: R is halo, loweralkyl(C -C loweralkoxy (C -C,), cyano, nitro, trifluoromethyl, phenylazo orp-chlorophenoxy; R, is hydrogen, halo, trifluoromethyl or loweralkyl(C,-C R is hydrogen or halo; and R is phenyl, halophenyl, dihalophenyl,alkyl (C -C phenyl, loweralkoxy (C C,) phenyl, l-naphthyl, 2-furyl, orZ-thienyl. It further relates to the novel hydrazone compounds thereofhaving unexpectedly high insecticidalactivity, having the formula:

wherein Y is hydrogen, chloro or loweralkyl (C -C n is 0, l or 2; and mis l or 2. Especially preferred compounds therein are: a,B-dioxo-,a-[(3-chloro-otolyl)hydrazone]hydrocinnamonitrile, a,B-dioxo-, a-[-(3,4-dichlorophenyl)hydrazone]hydrocinnamonitrile,

a,B-dioxo-, a-[ (2 ,4-dichlorophenyl )hydrazone ]hydrocinnamonitrile,p-chloro-a,B-dioxo, a-[(pchlorophenyl )hydrazone]hydrocinnamonitrile andchlorophenyl )hydrazone 2 hydrocinnamonitrile, a,B-dioxo-,oz-[(m-chlorophenyl)hydrazone]; hydrocinnamonitrile, a,B-dioxo-,a-[(o-chlorophenyl)hydrazone]; hydrocinnamonitrile, a,fl-dioxo-,a-[(4-chloro-o-tolyl)hydrazone]; hydrocinnamonitrile, a,B-dioxo-,a-[(2,5-dichlorophenyl)hydrazone]; hydrocinnamonitrile, p-chloro-a,/3-dioxo-, a-[(p-chlorophenyl)hydrazone]; hydrocinnamonitrile,a,B-dioxo-, a-(p-tolylhydrazone); Z-furanpropionitrile, a,B-dioxo-,oz-[(p-chlorophenyl)hydrazone]; 2-thiophenepropionitrile, a,B-dioxo-,a-[(p-chlorophenyl)- hydrazone]; 1-naphthalenepropionitrile, a,B-dioxo-,

-a-I(p-chlorophenyl)-hydrazone]; acetanilide, 4'-[(athetic method may beillustrated as follows:

0 u 1) R NO ax E 2) a cocn cm W III I wherein R is selected from thegroup consisting of an alkali metal, such as lithium, potassium orsodium and C -C loweralkyl groups, such as methyl, ethyl, npropyl,iso-propyl, n-butyl, t-butyl and the like and HX represents a mineralacid, such as l-lCl, H SO HNO and the like. R, R R and R are as above.

The relative quantities of the ingredients employed can be widelyvaried. For optimum yields, it is generally preferred to react equimolarquantities of the aniline and nitrite. Lower alcohols C -C water andmixtures thereof are among the preferred solvents for use in carryingout the synthesis. It is also preferred to employ a mineral acid insufficient quantities to produce an acidic pH in the aqueous oralcoholic solvent and to adjust the reaction temperature to temperatureswithin the range of from about 10C. to about +10C. The preferredtemperature is about 0C.

Sodium and potassium nitrite and methyl, ethyl or nbutyl nitrite areamong the preferred diazotizing agents which are particularly wellsuited for use in the syntheses.

Preferred mineral acids include sulfuric, hydrochloric and hydrobromicacid. It is generally preferred to employ a slight excess of the acidover and above the stoichiometric amount required to form thesubstituted benzene diazonium salt.

After formation of the desired diazonium salt, the reaction mixture ispreferably reacted further by adding it to a mixture of the appropriatearoylacetonitrile and a weak base, such as sodium or potassium acetatewhile the temperature is maintained at from about lC. to about +l0C. Thedesired hydrazone of the a,B-dioxohydrocinnamonitrile is producedthereby and may be recovered from the reaction mixture by any convenientmeans, such as, by filtration, centrifugation and the like.

It has been found that the hydrazones of Formula 1 and especially thenovel hydrazones a,B-dioxo-, a-[(3-chloro-o-tolyl)hydrazone]hydrocinnamonitrile and a,l3-dioxo-, a-[(3,4-dichlorophenyl)hydrazone]hydrocinnamonitrile are useful as insecticides. They are particularlyeffective for controlling lepidoptera and mosquitoes, especially in thelarval stages.

The insecticidal methods of the present invention involve contacting theinsect to be controlled or the locus or area where insect control isdesired with an insecticidally effective amount of one or more of saidhydrazones. Application of the active ingredient at a rate of frombetween about 0.5 and about 15 pounds per acre of the active ingredientis generally sufficient to achieve the desired insect control.

For application of the hydrazones, it is generally preferred to employthem in combination with conventional pesticidal adjuvants andformulation aids. They may be advantageously employed with the use ofeither solid or liquid adjuvants and applied in the form of dusts, dustconcentrates, wettable powders, emulsifiable concentrates and the like.

Field application of these formulations may be made by conventionalequipment, such as power dusters, boom and hand sprayers, spray dusters,addition to irrigation water, and the like.

The active ingredient may be initially formulated with a concentratedcomposition, comprising the active ingredient in a solid or liquidadjuvant which serves as a formulation aid or conditioning agent,permitting the concentrates to be further mixed with a suitable solid orliquid carrier.

Useful liquid adjuvants in which the toxicant is dissolved. suspended ordistributed include, for example, xylene, benzene, lower alcohols C,Cfuel oil or the like, with or without an emulsifying agent. Forapplication, the resulting solution can be further diluted with eitherwater or an organic diluent, such as deodorized kerosene. Concentrationsin the range of from about 5 to about 95 percent are generally suitablefor initial so- Q-NHZ NaNO H2S04 Qu N H804, CF CF;

lution. When diluted for application, suitable solutions may contain theactive ingredient in concentrations of from about 0.5 to about 5000 ppm.

Suitable solid adjuvants include, for example, attapulgite, kaolin, talcor diatomaceous earth in granular or finely ground form. The activeingredient can be conveniently formulated with the solid adjuvants asdusts, dust concentrates, wettable powders, granulars and the like.

Dusts are generally prepared by grinding together from about 1 to 10percent by weight of the hydrazone with a finely divided inert diluentsuch as attapulgite, kaolin, diatomaceous earth, talc, or fullers earth.These formulations can then be applied with dusting equipment to thefoliage of agronomic crops or fields, meadows, forests or the like whichare to be protected from insect attack or where insect control isdesired. Application is generally sufficient to provide between about0.5 and 15 pounds per acre of active material.

Dust concentrates are usually prepared in the same manner as dusts butgenerally from about 25 to percent by weight of the active hydrazone andfrom 75 to 25 percent by weight of diluent are used.

wettable powders are prepared in the same fashion as the dustconcentrates, however, from about 1 to 5 percent by weight of anemulsifying agent and from about 1 to 5 percent by weight of adispersing agent are usually included in such formulations. Polyethyleneglycols, methoxy polyethylene glycols, sodium lignosulfonate, calciumdodecylbenzene sulfonate and the like are among the emulsifying agentsand dispersing agents which can be used in these formulations. inpractice, the wettable powders are generally dispersed in water andapplied as a dilute spray to the vegetation or water where insectcontrol is desired.

Usually, concentrations of the active ingredient of from about 10 to1000 ppm dispersed in the water of ponds, lakes, creeks, swamps and suchwill give excellent control of mosquito larvae. Excellent insect controland plant protection in fields, forests, crop lands and the like isgenerally achieved by application of the active ingredient at rates offrom about 1 to about 15 pounds per acre.

The invention is further illustrated by the following examples which arenot to be taken as limitative thereof. In each case, the parts andpercentages are by weight unless otherwise indicated.

EXAMPLE 1 Preparation of a,B-dioxohydrocinnamonitrile a-(a,a,oz,a',a',a'-hexafluoro-3,5-xylyl )hydrazone NaOAc 0.02 mole) in Found EXAMPLE 1?Preparation of a,B-dioxo-a-[(p-chlorophenyl)hydrazone1-hydrocinnamonitrile C1 -N=C EXAMPLE 18 Preparation of a,B-dioxo-, a-[3-chloro-o-tolyl )hydrazone]hydrocinnamonitrile Analysts, percent Asolution of p-chloroaniline (2.5 g.

30 ml. of 10 percent aqueous hydrochloric acid was cooled to -5C., and asolution of sodium nitrite (1.5 g., 0.02 mole) in 5 ml. of water wasadded dropwise. The resulting solution was stirred for one-half hour.Excess nitrous acid was destroyed by addition of sulfamic 20 acid, andthe resulting solution was filtered. The filtrate was added dropwiseover a period of 15 minutes to a mixture of benzoylacetonitrile (2.9 g.,0.02 mole) in 30 ml. of methanol, ml, of water, and g. of solid sodiumacetate at 0C. The resulting mixture was stirred overnight. The desiredproduct was isolated by filtration, washed with water, and dried invacuo at 80C., yielding 5.0 g. (88 percent).

Purification was effected by successive recrystallizations from aqueousethanol to give a product having an m.p. of l175.5C.

in lieu of the TABLE I Percent Yield c.)

Calcd. for C l-l F N O: C, 53.00; H, 2.35; F, 29.59; N, 10.91. Found: C,52.77; H, 2.33; F, 30.55; N, 10.92.

EXAMPLES 2-16 Preparation of various a,B-dioxohydrocinnamonitrilehydrazones A variety of a,B-dioxohydrocinnamonitrile hydrazones ofFormula 1 were prepared by the general procedure of Example 1, employingthe appropriately substituted aniline and cinnamonitrile,

'tated as a flocculent white solid. This mixture was stirred andmaintained in an ice bath while a solution of the sodium nitrite (1.72g., 0.0250 mole) in a little water was added dropwise. The yellowdiazonium salt solution was then filtered to remove a small amount of 5precipitate. The B-oxohydrocinnamonitrile (3.62 g., 0.0250 mole) wasslurried in 25 ml. of 28 ethanol. and

a solution of sodium acetate (12.30 g., 0.150 mole) in 40 ml. of waterwas added. This mixture was stirred and maintained in an ice bath whilethe diazonium salt solu- 10 tion was added dropwise. Thereafter, thesolution was stirred with cooling for an additional hour and the desiredproduct produced as a solid precipitate was recovered by filtration. Itwas washed with water, and air dried to yield 8.07 g. (84 percent yield)in the form of 15 a yellow-orange solid having an m.p. of l85-l9lC. Theproduct was purified and recrystallized from ethanol with a little addedwater to yield 5.93 g. (62 percent) of a yellow-orange solid having anm.p. of l9l.0-193.5C. Identification was by infrared spectrum and thefollowing elemental analysis:

a,a,a,a',a',a-hexafluoro-3,5-xylidene and B-oxohydrocinnamonitrile usedtherein, to produce the hydrazones set forth in Table I below. R whichis shown in 35 Table l, is in each case l-l.

Cl H

/ ENC16 NH; HCl KNO .Ste I Dec.

manna m mm mm m m mmmnma mum u m m "Humane now an muuummm mun mnmm newun 22a 11$ magma mun nmmm mnmmaum nun uunn www mm no M Human m mum m m Hmmuummm awn use mmnumnn mum mmmm ame: can an: LllLlZL Z21 call Manamaman can nanuunu mum awn mmmmmmm H H mm. n 1 111 mmmll l l m emnumww 3.Mama W m 1.1.; a lzzm mmmmamm $88 nnewnn nnnenenw m. m B N .|C

0H0 mmm w mmmmmw 2" Lmmmmmmu added dropwise, maintaining the temperatureat C. The diazonium salt solution was then added to a solution of 5.81grams (0.04 m.) of benzoylacetonitrile and 30 grams (0.365 m.) of sodiumacetate dissolved in 300 ml. of water and 200 ml. of methanol, overapproximately minutes with rapid stirring at room temperature. Themixture was stirred for 1 hour at room temperature, and the brightyellow solids were collected by filtration. The crude product wasrecrystallized from 300 ml. of ethanol to 50 ml. of methyl ethyl ketone,water was added at reflux until the cloud point was reached(approximately 50 ml. necessary). 9.45 grams (80 percent theory) ofyellow needles were obtained. Melting point is 133 to 133.5C.

Analysis. Calculated for N OCIC H C, 64.56; H, 4.03; N, 14.12. Found: C,64.16; H, 4.00; N, 14.08.

As in the case of the preparation of a,B-dioxo-,a-[(3-chloro-o-toly1)hydrazone] hydrocinnamonitrile, the other novelhydrocinnamonitrile insecticides mentioned above, e.g., a,B-dioxo-,phenyl)hydrazone] hydrocinnamonitrile, can also be prepared by reactingthe appropriately substituted aniline at a temperature of from aboutl0C. to about +C. with a compound of the formula R NO in a solventrendered acidic by the addition of a mineral acid to form a diazoniumsalt solution of said aniline, and reacting the diazonium salt insolution to form said hydrazone by adding said diazonium salt to amixture of a weak base and an aroylacetonitrile, e.g.,

wherein R is a member selected from the group consisting of alkalimetals and C -C loweralkyl groups.

Step 2 Cl CH NEN CP cocn c m NaOAc ESE/l) 5.66 grams (0.04 m.) of3-chloro-o-t0luidine was dis- E solved in 60 ml. of 3N HCl (0.186 m.),and the solution XAMPFE 19 was cooled to 36 grams (004 m) of potassiumPreparation of various afi-dtoxohydrocinnamonitrile nitrite, which wasdissolved in 10 ml. of water, was then hydrazones A variety ofa,B-dioxohydrocinnamonitrile hydrazones of Formula I were prepared bythe general procedure of Example 1, employing the appropriatelysubstituted aniline and cinnamonitrile. The compounds produced are setforth in Table 11 below.

TABLE II 0 Bl -Rg NHN==C Bi CN R B: Ra

Z-Cl 8-0] H Z-Cl. H

bra-04H K Z-CH: H

S-CL H mm H 8-CFa 6-CF H G-CICuHsO H H EXAMPLES 20-33 The insecticidalactivity of the compounds of Formula I is demonstrated by the followingtests using the test procedures set forth below.

Southern Armyworm (Pradenl'a eridania Cram.)

beaker containing 25 ml. of water. The test compound is formulated as anemulsion containing 0.1 gram of test material, 0.2 gram of Alrodyne 315emulsifier, a nonionic polymeric emulsifier by Alrose Chemical Company,ml. of acetone and 90 ml. of water. This 1000 ppm emulsion is dilutedten-fold with 65 percent acetone'35 percent water to give 100 ppm. Onemilliliter of the 100 ppm emulsion is pipetted into 225 ml. of water ina 400 ml. beaker and stirred vigorously. The

f zm i g' g i' aretmade. i as periem 10 larvae in 25 ml. of water areadded, giving a concentra- T m th a W i i g i i i tion of 0.4 ppm.Mortality counts are made after 24 e311 eaves ire di d ppim l g 3 es T fhours at 80F. Data obtained are provided below in F a 9 ey are P Tablew. R which is unshown in Table IV below, is petrl dlshes llned on thebottom wlth a molst filter 'ln each case H. paper and tenthlrd-lnstararmyworms are added to each dish. The dishes are covered,held at 80F, 60 percent relative humidity for 2 days and then examinedTABLE IV and mortallty counts made. Untreated leaves are used ascontrols. Kill,

Ex. Mosquito Larvae,

No. R R, R2 Concentration 0.47: To a E w b Coo ud Orm 34 m-Cl H phenyl92 H I h H 2Cl 5Cl phenyl s reseus) 36 2CH3 4Cl phenyl lOO Compounds tobe tested are made up as 0.1 percent 37 =l 2 phenyl 76 1 ti /35 t t t SIn 25 38 Benzo phenyl 100 so u ons ln ace one-waer mnr ures. ma eaves 39H p chk,mphcnyl 100 from cotton plants are then dlpped 1n the selectedtest 40 p I H lhieflyl 100 solutions and air dried. After drying, theyare placed in 2; g:% S 82? 82 a small medicine cup with a dental wicksaturated with water and one third-instar tobacco budworm and held 30 ina constant temperature and humidity room for 3 da s. A t nd of theholdin eriod all cu s ar ext he 6 g p p e EXAMPLE 43 amlned andmortallty counts made. At least 10 repli- Cates per test Solution rused- Foliar Residual Activity of Phenylhydrazones The data obtalned arem each case set forth m Table lll below. R which is unshown in TableIII, is in each The foliar residual activity of the phenylhydrazonescase H. and commercial standards is shown in Tables V, VI, VII- TABLEIll 74 Control Ex. Soutllem Armyworm, Tobacco Budworm, No. R R R2Concentration 0. l9? Concentration 0.1%

20 p-Cl H phenyl lOO 90 21 m-Cl H phenyl lOO 22 2-Cl 5Cl phenyl lOO 9O23 p-Cl 0---CH phenyl 100 24 pCH H phenyl 9O 6O 25 --cl-l 5 No phenyl 6026 Benzo phenyl 50 60 27 p-Cl H p-chlorophcrlyl l 00 2s p-Cl H furyl 10060 29 p-Cl H thicnyl 100 80 3O p-Cl H naphthyl I00 90 31 3CF 1 5CFphenyl lO0 100 32 p-Cl H. a 100 100 33 p-phenylazo H phenyl l00 100EXAMPLES 34-42 The larvicidal activity of the compounds of Formula 60 lis demonstrated in the following tests using mosquito larvae. The testprocedure is as follows:

Mosquito Larvae (Anopheles quadrimaculalus Say) Groups of 25 larvae ofthe common malaria mosquito are transferred with a medicine dropper to a50 ml.

lent of 86 gallons per acre. Following application, the treated plantsare placed on greenhouse benches and permitted to dry. At various timeintervals thereafter, treated leaves are removed from the plants, placedin petri dishes with moist filter papers on the bottoms thereof andcontaining or southern armyworms or gypsy moth larvae. Mortality countsare made after 3 days of exposure.

For bioassays with tobacco budworms, the excised leaves are cut intofive sections, and each section is placed in a 1 ounce plastic medicinecup containing a 1 inch dental wick saturated with water, and one-thirdlnstar tobacco budworm. Mortality counts are made after 3 days ofexposure.

TABLE V Fuller residual activity 0! phenylhydmzonaa on lime bean plantsblnmyod with southern armywarma o! mfldna Rate, on 1 in pounds per 0 2 84 we Percent nma'tality Formmatlon Structure w? as COZ=NNHCI 1 no no 109100 %WP-ChecL o o o 0 W1 14 50 m 50% -C0(|J=NNH-Cl 1 so m 20 Cu'N w c114 so 49 50% 1) 1 so so as :0 as so so mm c 1 100 a) so so mwr-chwk m a)o no TABLE VI Follar residual activity of phenylhydramnea on time beanplants Eyed with southern arm oltmpinnta 30% m in m par 9 l 8 8 an FStructure PM mummy 1s 100 ea 78 m 1 1m 16!) um l 1m 89 t8 1 m1 260 76 moE 1m 1m (-25 1 109 mu m 16B TABLE JUL-Continued Felts: residual wtlvityof experimental umecticic'tea and standards on cotton plants aged in thegreenhouse and btomyed with various Insects Age of residue on plants tnweeks Tobacco budwomr Bentham srmyworm Gypsy moth larvae Rate,pounds013801284'0128 Formupar latlon Structure acre Percent mortalityafter 8 days of %WP k 13 2E 53 0..-.. $0 75 25... 1100mm)0..-..16090809912557510 0 aoaaeacasowomoeseoaatmomoeiefleomnmlwmesmrmmea M100 m to n mo mo m0 100 weamoraworaromoicomomm 1 Southern armywcxms mall-used second luster, notthird.

EXAMPLE 44 EXAMPLE 45 Field Evaluatlon of Test Compounds 30 Theeffectiveness of the phenylhdrazone in the con- Test materials wereapplied at the rate ofl pound actrol of imported cabbage worm (Pierisrapae) on 3 ltual ingredient in 57 gallons of water per acre.Applicafoot rows of cabbage was determined using the application wasmade by a C0 power-pack sprayer with three tion procedure of Example 44.The results obtained are flat-tip spray nozzles at a pressure of 25p.s.i. and at a 3 set forth in Table X below.

TABLE X amma structure Emulation cabham CmN 5 1% WP 1.0 a-oo--o=rs--NH--c1 Control 6.7

50 tractor speed of4 miles per hour. The foliage of 60-foot EXAMPLE 46rows of potatoes were treated on schedule for control of Colorado PotatoBeetle (Leptinomrsa decemlineata Effectiveness of test compounds againstinsects of the The data obtained for the test compound and untreatedOrder C0 P r8 i5 ShOWn m the follo ing testcontrol are set forth inTable IX below, 55 The test procedure employed to determine the effi-TABLE IX 2 Fatal 1 Ln "'3 Formatu potato v Stream Lama 524mm lea/rowTABLE XI Ule oi eevenl phenylhydruonee ended! where Y is hydrogen,chloro or lower alkyl (C -C cucumber beetle (Diabiotfee net adultspotted panama houmdi) and 531i Mexican been beetle (Epiladma animus)Adult Adult Conapotted Mexican centntion cucumber bean Structure inp.p.m. beetles beetle Cl M GEN 80 100 co-i:=N-Nn 01 G1 I, 80 50 C=Nco-c=n-xm c1 CH 01 LG 80 50 C=N O0-c=N-NH GEN 1.000 so an ooo-e=N-Nn--o124:7 mortality data. 4-day mortality data.

EXAMPLE 47 m is l or 2; and

nis0,lor2.

2. The compound of claim 1, a,B-dioxo-, (ll-[(3- chloro-o-tolyl)hydrazone]hydrocinnam0nitrile.

3. The compound of claim 1, a,B-dioxo-a-[(3,4-

4O dichlorophenyl)hydrazone]hydrocinnamonitrile.

4. The compound of claim 1, p-chloro-a,B-dioxo-,a- [(p-chlorophenyl)hydrazone hydrocinnamonitrile.

TABLE X11 U oi drew in i liar treatment in ileld control 0! the (allermyworm m (Spodopt mfrupipcrdd) oneorn is ental Total 118!- wormsFamedientper intluee Structure letien we replicate.

GEN 60%WP... 1 76 ool=N-m1--ci O1 50%WP... l 19 GEN ool'=N-NH can mm...1 ae c1-C -co-l:=N-Nn- 01 0mm as 65 v We claim: 5. The compound of claim1, p-chloro-a,B-d1oxo-al. A hydrocinnamonitrile compound having theformula:

[phenylhydrazone]hydrocinnamonitrile.

1. A HYDROCINNAMONITRILE COMPOUND HAVING THE FORMULA:
 2. The compound ofclaim 1, Alpha , Beta -dioxo-, Alpha-((3-chloro-o-tolyl)hydrazone)hydrocinnamonitrile.
 3. The compound ofclaim 1, Alpha , Beta -dioxo- Alpha-((3,4-dichlorophenyl)hydrazone)hydrocinnamonitrile.
 4. The compound ofclaim 1, p-chloro- Alpha , Beta -dioxo-, Alpha-((p-chlorophenyl)hydrazone)hydrocinnamonitrile.
 5. The compound ofclaim 1, p-chloro- Alpha , Beta -dioxo- Alpha-(phenylhydrazone)hydrocinnamonitrile.